Hydrochloric Acid → 2-Ethoxy-4-methoxybenzoic acid

HRID 2263937Notes

Reaction equation

HRID 2263937 reaction equation
C([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH2:14][CH3:15])C.[OH-].[K+].Cl>C(O)C>[CH2:14]([O:13][C:6]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=1[C:4]([OH:16])=[O:3])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 670715012-Ethoxy-4-methoxybenzoic acid ethyl ester

Product 1

HCID 134507622-Ethoxy-4-methoxybenzoic acidYield 83.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Ethoxy-4-methoxybenzoic acid ethyl ester (13 g, 58 mmol) was suspended in ethanol (150 mL). This was treated with potassium hydroxide (40 mL, ˜4 M) and refluxed for 1 h. The reaction was cooled and poured into cold aqueous hydrochloric acid (300 mL, 2 M) and extracted into dichloromethane (3×200 mL). The organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solids were filtered off, and the filtrate was evaporated to dryness to give 2-ethoxy-4-methoxybenzoic acid (9.5 g, white solid).

Workup

  1. temperaturerefluxed for 1 h
  2. temperatureThe reaction was cooled
  3. extractionextracted into dichloromethane (3×200 mL)
  4. washThe organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solids were filtered off
  7. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6fd262c76ba342159226eab828976f53
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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